How realistic is it to move from an in-house counsel role to the business side (strategy / finance / sales)

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Pretty unrealistic in my estimation. If you wanted to be a financier, you'd probably be one already. If you really want to make the transition and you have the skills and pedigree and network, then you'll be able to do it.

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If you're that guy, then totally realistic. But for most people it's just a pipe dream.

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Friend of mine was a mid level litigation associate, moved into insurance sales and is much happier. Definitely possible, but as C1 noted it’s more of an easy reality for those with great charisma (hopefully you do!)

The former GC at my company now works in strategy but he took a big demotion to do it

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